2-[(2Z)-3-(3,4-dimethoxyphenyl)prop-2-enamido]benzoic acid

• ChemBase ID: 178828
• Molecular Formular: C18H17NO5
• Molecular Mass: 327.33128
• Monoisotopic Mass: 327.11067265
• SMILES: c1cc(c(cc1)NC(=O)/C=C\c1cc(c(cc1)OC)OC)C(=O)O
• Canonical SMILES: COc1cc(/C=C\C(=O)Nc2ccccc2C(=O)O)ccc1OC
• InChI: InChI=1S/C18H17NO5/c1-23-15-9-7-12(11-16(15)24-2)8-10-17(20)19-14-6-4-3-5-13(14)18(21)22/h3-11H,1-2H3,(H,19,20)(H,21,22)/b10-8-
• InChIKey: NZHGWWWHIYHZNX-NTMALXAHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(2Z)-3-(3,4-dimethoxyphenyl)prop-2-enamido]benzoic acid
• IUPAC Traditional name: 2-[(2Z)-3-(3,4-dimethoxyphenyl)prop-2-enamido]benzoic acid
• Synonyms: 2-[[(2Z)-3-(3,4-Dimethoxyphenyl)-1-oxo-2-propen-1-yl]amino]benzoic Acid; (Z)-2-[[3-(3,4-Dimethoxyphenyl)-1-oxo-2-propenyl]amino]benzoic Acid; cis-Tranilast

Database IDs

• CAS Number: 91920-58-0
• PubChem SID: 164234738
• PubChem CID: 6604021

CALCULATED PROPERTIES

• Acid pKa: 3.5528402
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 1.6218046
• LogD (pH = 7.4): 0.20370603
• Log P: 3.5626285
• Molar Refractivity: 91.5198 cm^3
• Polarizability: 33.853416 Å^3
• Polar Surface Area: 84.86 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - T714560

Antiallergic drug, used to treat bronchial asthma, allergic rhinitis and atopic dermatitis.

REFERENCES

• Shiota, N., et al.: Brit. J. Pharmacol., 159, 626 (2010)
• Gohil, V., et al.: Nat. Biotechnol., 28, 249 (2010)
• Kawabata, Y., et al.: Eur. J. Pharm. Sci., 39, 256 (2010)